Cumnundrum 

When you have to think too hard about where to deposit your own semen. Or as I like to say: "When you really, really aren't sure where to put your slick little boys!".

"She told me she was on the pill, and yet I should have been wearing a condom anyway, and then she kept saying 'cum inside me!, cum inside me!'". It was quite the cumnundrum.
Example two: I started jerking off watching porn in my grandma's basement, and right before I was about to cum I ran into the bathroom for some toilet paper and I realized my grandfather was in there with diarhea. Dude, it was quite the cumnundrum.

Cumnundrum by Scooby Blue June 8, 2009

cumnundrum 

When two consenting adults opt out of sex because their kids run in the same circles.

Wow. This is hot, but we're in a serious cumnundrum. We cannot have sex. Our kids have 8 years of school left together and I'm averse to extended awkwardness.

cumnundrum by freegrrrl October 14, 2012

The Aquaman Conundrum

In film, books, and television, when the day can conveniently be saved by a very specific skill possessed by the protagonist.

See any Aquaman story where the world is saved by talking to fish.

Coined by Marc of Angry Puppy.

The film 10,000 BC had a bad case of the Aquaman Conundrum.

The Aquaman Conundrum by V. Ampersand August 24, 2008

dodo’s conundrum 

When you have the means to do something but still can’t do it. A dodo bird has wings but could not fly. Some would also describe this as not understanding why you can’t achieve a particular goal.

Giuseppe: I have done all the homework and been listening in class and gone to tutoring but i still can’t seem to pass the class
Amy: Wow it sounds like you’re facing the dodo’s conundrum

dodo’s conundrum by brosifer November 14, 2019

Cuntundrum 

1. An unsolvable issue or problem with your wife or girlfriend.

2. A catch-22 involving a woman

That's quite a cuntundrum. I'm glad I'm not in your shoes.

Cuntundrum by fullaflex March 21, 2011

Coitus Conundrum 

When you are in a sistuation with two or more hot girls, and you can not identify the hotter girl or whichone you would sleep with.

Dave: Look at all these hot chicks!

Steve: Which one would you sleep with?

Dave: All of them.

Steve: Yeah, but if you had to pick just one.

Dave: ... (Coitus Conundrum)

Coitus Conundrum by Bagseven May 20, 2010

hipster conundrum 

The paradoxical concept that most hipsters now find themselves in - the fact that to be a hipster is to oppose all things mainstream, but now being hipster is mainstream.

Damn, I canz not be hipster anymore, too mainstream! Damm hipster conundrum haz I...

hipster conundrum by captain capable November 14, 2012